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I V",

288

PRACTICAL ORGANIC CHEMISTRY

i.

of phenylhydrazine on ethyl acetoacetate, is acted upon with
methyl iodide.   The two reactions are represented as follows :—

CH.,.CO.CH«.COOCoHB   CIL.C~-CHo.CO

"I           + HoO +

N

N.CGH5

-- N.C6H5

Phenylmethylpyrazolone.

CH8.G=CH.CO
+CH3I=         |           |

CII3.N -- N.C6H5

Phenyldimethylpyrazolone
' (antipyrine).

The variety of syntheses into which phenylhydrazine enters
cannot be described here ; but reference must be made to the
text-book.

It should be noted that the action of phenylhydrazine on
the ketone group, and of diazobenzene salts on the methylene
group situated between two CO groups, are analogous to that
'of hydroxylamine and nitrous acid upon these two groups, of
which the following are examples : —

CO.OCoH5

I
CO

I

Mesoxalic
ester.

COOCoIi,

CI-lo

!

COOCoH5 xv

Succinic            + 0:NOH

ester.

COOC.HB

I

-f NH.,NHCGH5 = C:N.NH.QHfi + H2O

COOG,HB

NHoOH

C1N:N.C6H4 =  C:N.NII.C6H5 + HCL
COOC2H5

= CtNOII + HoO
COOCoIi,

COOC,H5
C:NOH

HoO

COOC3H5
Phenylhydrazine has been used in the synthesis of indole
derivatives.    The hydrazones of aldehydes and ketones contain-